Chestertown, Maryland Homes For Sale & Real Estate

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Real Estate Homes For Sale In Chestertown, MD

Beautifully maintained home tucked away on a quiet cul-de-sac but still within walking distance to downtown shops, restaurants, and riverfront. Open floor plan with 9ft ceilings in the living room. 3 bedrooms and 2 full bath with a 2 car attached....

CHESTERTOWN Homes |

MLS #MDKE2004172

Single Family Residence

$530,000 | Active Home listing

3 Beds | 2 Baths | 1,467 Sqft | 0 Acres Lot

217 RADCLIFFE DRIVE, CHESTERTOWN, MD 21620 KENT County

Real Estate Details & Photos
Looking for extra space? This home has a large extra room  that could be a primary bedroom & bath with walk in closet, a den/playroom, office with a separate private entrance, gym or whatever your lifestyle is in need of! The original primary....

CHESTERTOWN Homes |

MLS #MDKE2004130

Single Family Residence

$284,000 | Active Home listing

4 Beds | 3 Baths | 1,632 Sqft | 1 Acres Lot

305 LINCOLN DRIVE, CHESTERTOWN, MD 21620 KENT County

Real Estate Details & Photos
Investor Alert! A rare opportunity to own a piece of History in down town Chestertown! This home has been a very lucrative rental for the past 10 years which you can easily add to your portfolio or rennovate and bring it back to its glory! One of....

CHESTERTOWN Homes |

MLS #MDKE2004134

Single Family Residence

$272,500 | Active Home listing

3 Beds | 2 Baths | 1,234 Sqft | 0 Acres Lot

631 HIGH STREET, CHESTERTOWN, MD 21620 KENT County

Real Estate Details & Photos
Discover your dream home nestled in a serene water-privileged community with exclusive access to a boat ramp, a small marina, and picturesque walking trails. This inviting 3-bedroom, 2-bath residence offers an ideal blend of comfort, convenience,....

CHESTERTOWN Homes |

MLS #MDKE2004144

Single Family Residence

$359,000 | Active Home listing

3 Beds | 2 Baths | 1,789 Sqft | 1 Acres Lot

23120 CLUB TERRACE, CHESTERTOWN, MD 21620 KENT County

Real Estate Details & Photos
This beautiful custom home on an acre of land has 4 Beds and 2.5 baths.  There is an eat-in-Kitchen with granite countertops that is completed by the Maple Wood Island, Gas cooking, and stainless steel appliances, soft close cabinets and 2....

CHESTERTOWN Homes |

MLS #MDKE2004056

Single Family Residence

$450,000 | Active Home listing

4 Beds | 3 Baths | 2,240 Sqft | 1 Acres Lot

8500 BROAD NECK ROAD SW, CHESTERTOWN, MD 21620 KENT County

Real Estate Details & Photos
Looking for something truly special? Don't miss this unique offering, located in the vibrant heart of Chestertown's Historic and Arts & Entertainment Districts! 
Boasting a legacy of over half a century under the stewardship of one devoted family,....

CHESTERTOWN Homes |

MLS #MDKE2004076

Townhouse

$425,000 | Active Home listing

7 Beds | 4 Baths | 3,664 Sqft | 0 Acres Lot

349 HIGH STREET, CHESTERTOWN, MD 21620 KENT County

Townhouse Details & Photos
Well maintained Cape Cod in the sought after Coventry Farms subdivision in Chestertown - 1st Floor Master Bedroom includes a spacious walk in closet and a large Full Bath with Walk in Shower – 4 bedrooms, 2.5 baths, a spacious living room, and a....

CHESTERTOWN Homes |

MLS #MDKE2004066

Single Family Residence

$360,000 | Active Home listing

4 Beds | 3 Baths | 2,472 Sqft | 0 Acres Lot

213 DEVON DRIVE, CHESTERTOWN, MD 21620 KENT County

Real Estate Details & Photos
Welcome to a captivating opportunity to reside in the idyllic neighborhood of The Grove in picturesque Queen Anne's County. Prepare to be enchanted by this charming abode, where every detail exudes warmth and comfort.

Step inside and be greeted....

CHESTERTOWN Homes |

MLS #MDQA2009698

Single Family Residence

$515,000 | Active Home listing

4 Beds | 3 Baths | 2,864 Sqft | 1 Acres Lot

112 SHEAFFER ROAD, CHESTERTOWN, MD 21620 QUEEN ANNES County

Real Estate Details & Photos
Step inside this stately brick colonial to see and feel the quality of this stunning renovation in Chestertown's vibrant historic district!  From the five piece luxury bath in the owner's suite, to the full guest apartment on the third floor, no....

CHESTERTOWN Homes |

MLS #MDKE2003972

Single Family Residence

$879,000 | Active Home listing

4 Beds | 4 Baths | 3,355 Sqft | 0 Acres Lot

307 WASHINGTON AVENUE, CHESTERTOWN, MD 21620 KENT County

Real Estate Details & Photos
This circa 2011, white brick house was built to celebrate the expansive views over the  Chester River Yacht &Country Club golf course to the Chester River. There is an attractive patio at one end and a screened porch off the owner's suite. The....

CHESTERTOWN Homes |

MLS #MDKE2003814

Single Family Residence

$975,000 | Active Home listing

4 Beds | 3 Baths | 4,730 Sqft | 1 Acres Lot

7755 WATERVIEW LANE, CHESTERTOWN, MD 21620 KENT County

Real Estate Details & Photos
Wonderful renovation, modern, efficient, and move in ready!   Home features vaulted ceilings with open flexible floorplan and 2 brand new luxury bathrooms.   Energy efficient instant hot water heater.  Large side deck, plenty of parking, small....

CHESTERTOWN Homes |

MLS #MDQA2009482

Single Family Residence

$289,000 | Active Home listing

2 Beds | 2 Baths | 864 Sqft | 1 Acres Lot

235 BURCHARD SAWMILL ROAD, CHESTERTOWN, MD 21620 QUEEN ANNES County

Real Estate Details & Photos
Step into a world of timeless elegance and tranquility with this meticulously maintained retreat. As you turn into the Fairgale Subdivision, it feels as though you are entering an estate, with majestic trees lining both sides of the paved road,....

CHESTERTOWN Homes |

MLS #MDKE2003704

Single Family Residence

$1,300,000 | Active Home listing

5 Beds | 5 Baths | 6,459 Sqft | 4 Acres Lot

22956 FAIRGALE FARM LANE, CHESTERTOWN, MD 21620 KENT County

Real Estate Details & Photos
Well maintained 2 bedroom 1 bath Colonial on .69 acres with winter water views of Fishing Creek! Features Include: Screened Porch * 1-Car Attached Garage * Tilt-in Insulated Double Pane Windows  * Large Living / Dining Room Combo with Brick....

CHESTERTOWN Homes |

MLS #MDQA2009122

Single Family Residence

$269,900 | Active Home listing

2 Beds | 1 Baths | 1,408 Sqft | 1 Acres Lot

332 TRUSLOW ROAD, CHESTERTOWN, MD 21620 QUEEN ANNES County

Real Estate Details & Photos
Welcome to your tranquil retreat at Orchard Hill, where modern sophistication meets peaceful living on 1.89 acres of beautifully landscaped grounds. This stunning Cape Cod style home offers an abundance of amenities and thoughtful details....

CHESTERTOWN Homes |

MLS #MDKE2003556

Single Family Residence

$498,000 | Active Home listing

2 Beds | 3 Baths | 2,210 Sqft | 2 Acres Lot

8757 ORCHARD DRIVE, CHESTERTOWN, MD 21620 KENT County

Real Estate Details & Photos
Price improvement! Two perfectly adorable cottages in Tolchester.  Both were completely remodeled.  The cottages sit on 3 lots totaling about .46 acres. Each has one bedroom, a full bath, kitchen and living areas. The front cottage also has an....

CHESTERTOWN Homes |

MLS #MDKE2003374

Single Family Residence

$279,900 | Active Home listing

2 Beds | 2 Baths | 1,150 Sqft | 0 Acres Lot

9020 CUMBERLAND STREET, CHESTERTOWN, MD 21620 KENT County

Real Estate Details & Photos
SMITH-RINGGOLD HOUSE. ca. 1750    
OWNER IS MEETING THE MARKET  for this rare property WITH PRICE NOW AT $1,6500,000. 
  
This exceptional property is a rare find: an authentic waterfront 18th century home with 21st century comfort in heart of....

CHESTERTOWN Homes |

MLS #MDKE2002790

Single Family Residence

$1,650,000 | Active Home listing

4 Beds | 5 Baths | 5,195 Sqft | 0 Acres Lot

201 N WATER STREET, CHESTERTOWN, MD 21620 KENT County

Real Estate Details & Photos

Chestertown, MD Real Estate Home Trends

Kent County Buy Statistics

  • Total Housesolds
  • 8,375
  • Median Home Value
  • $291,900
  • Median Housing Costs
  • $1,781
  • Median Household Income
  • $71,635
  • Median Real Estate Taxes
  • $Not Available
  • Homes With Primary Mortgage Only
  • Not Available%
    • Homes With Second Mortgage
    • Not Available%
    • Homes With Home Equity Mortgage Only
    • Not Available%

    Chestertown Types of Homes for Sale

    Chestertown Real Estate Listings

    Chestertown, MD Homes Prices

    • Total Housesolds
    • 8,375
    • Median Home Value
    • $411,900
    • Median Housing Costs
    • $2,097
    • Median Household Income
    • $94,991
    • Average Household Income
    • $125,876
    • Median Real Estate Taxes
    • $3,857
    • Homes With Primary Mortgage Only
  • 86.9%
    • Homes With Second Mortgage
    • 10.6%
    • Homes With Home Equity Mortgage Only
    • 2.5%
    • Total Population
    • 6,164,660
    • Median Age
    • 39.7
    • Male To Female Ratio
    • 95.1
    • Average Household Size
    • 2.76
    • Median Rent For House
    • $1,550
    • Owner-Occupied House Units
    • 67.7%
    • Renters Occupied House Units
    • 32.3%

    Real Estate Home Mortgage Loan Rates Chestertown Maryland

    Home loan finance mortgage calculator to find Maryland real estate payment calculations

    Housing Calculator Affordability

    About Chestertown

    • Chestertown has total households of 8,375 with a real estate for sale median home value of $291,900 compared to the state median home price of $411,900. The median real estate taxes paid are $Not Available and the household income is $71,635. Not Available% of Chestertown homes with a mortgage have no second mortgage or home equity line of credit. Chestertown Maryland home types of MLS housing to buy including single family homes, condos, townhomes, residential studio, apartment, townhouse, and multi-family houses.

    Chestertown Neighborhoods

    What Zip Codes in Chestertown have homes for sale listing?

    City neighborhood housing zip codes have MLS listing homes for sale within Chestertown, MD for buyers: 21620, 21690.

    Chestertown Local Economy & Job Opportunities

    The median household income is 71,635 and the median state household income is 94,991. The average household income is 125,876 in Maryland.

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